Hydrochloric Acid → HCID 10178449, compound

HRID 2120137Notes

Reaction equation

HRID 2120137 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Al](C)C.CO[C:13]([C:15]1[CH:16]=[C:17]([NH2:30])[C:18]2[N:19]([N:21]=[C:22]([C:24]3[O:25][C:26]([Br:29])=[CH:27][CH:28]=3)[N:23]=2)[CH:20]=1)=[O:14].Cl>O1CCOCC1.C1(C)C=CC=CC=1>[NH2:30][C:17]1[C:18]2[N:19]([N:21]=[C:22]([C:24]3[O:25][C:26]([Br:29])=[CH:27][CH:28]=3)[N:23]=2)[CH:20]=[C:15]([C:13]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:14])[CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 16682925TrimethylaluminumHCID 69926968HCID 69926968, compound

Product 1

HCID 10178449HCID 10178449, compoundYield 29.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 20 mg (0.24 mmol) piperidine in 1 ml dioxane was treated with 0.24 ml (0.24 mmol) trimethylaluminum in toluene and stirred for 1 h at room temperature. 20 mg (0.06 mmol) 8-Amino-2-(5-bromo-furan-2-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid methyl ester in 1 ml dioxane was added and the mixture was heated to 90° C. for 72 h. 0.5 ml 1N HCl aq. was added and the volatiles were removed. The residue was taken up in 1.5 ml formic acid and 0.5 ml methanol and purified by reversed phase preparative HPLC eluting with a gradient of acetonitrile and water. The elution solvents were evaporated to obtain 7 mg (29%) of the title compound.

Workup

  1. temperaturethe mixture was heated to 90° C. for 72 h
  2. customthe volatiles were removed
  3. custom0.5 ml methanol and purified by reversed phase preparative HPLC
  4. washeluting with a gradient of acetonitrile and water
  5. customThe elution solvents were evaporated

Sources & evidence

ORD record
ord-f28779170e094ac0a624a8fce8c5a3f8
Source dataset
uspto-grants-2004_02
Patent number
US06689790B2

Reaction notes

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